Hydrochloric Acid → 2-[1-[[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-phenylmethoxyoxan-3-yl]amino]ethylidene]-5,5-dimethylcyclohexane-1,3-dione

HRID 991144

Reaktionsgleichung

Reaktionsgleichung von HRID 991144
C([NH:4][C@@H:5]1[C@@H:18]([OH:19])[C@H:17]([OH:20])[C@@H:16]([CH2:21][OH:22])[O:15][C@@H:6]1[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=O)C.Cl.[CH3:24][C:25]([CH:27]1[C:33](=[O:34])[CH2:32][C:31]([CH3:36])([CH3:35])[CH2:30][C:28]1=[O:29])=O.C(N(CC)C(C)C)(C)C>[OH-].[Na+]>[CH3:35][C:31]1([CH3:36])[CH2:32][C:33](=[O:34])[C:27](=[C:25]([NH:4][C@@H:5]2[C@@H:18]([OH:19])[C@H:17]([OH:20])[C@@H:16]([CH2:21][OH:22])[O:15][C@@H:6]2[O:7][CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH3:24])[C:28](=[O:29])[CH2:30]1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 5194481,3-Cyclohexanedione, 2-acetyl-5,5-dimethyl-HCID 2801971Benzyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside

Produkt 1

HCID 1784645382-[1-[[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-phenylmethoxyoxan-3-yl]amino]ethylidene]-5,5-dimethylcyclohexane-1,3-dioneAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

A solution of Benzyl 2-Acetamido-2-deoxy-α-D-glucopyranoside (4.70 g, 15.11 mmol) in 1 M NaOH solution was refluxed at 120° C. for 15 h. The reaction mixture was cooled to room temperature, neutralised with 1 M HCl solution and concentrated. The residue was dissolved in dry ETOH (50 ml) and filtered. 2-Acetyldimedone (4.11 g, 22.6 mmol) and N,N-diisopropylethylamine (2 ml) were added to the filtrate, and the mixture was refluxed for 2 h. The reaction mixture was evaporated to dryness, and the residue was taken up in EtOAc (50 ml), washed with 1M KHSO4 solution, brine, and evaporated to give Benzyl 2-Deoxy-2-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethylamino]-α-D-glucopyranoside (7) (3.78 g, 58%).

Aufarbeitung

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in dry ETOH (50 ml)
  3. filtrationfiltered
  4. temperaturethe mixture was refluxed for 2 h
  5. customThe reaction mixture was evaporated to dryness
  6. washwashed with 1M KHSO4 solution, brine
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-9ddce6e0cd634ec9bc69880de9911c82
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06462183B1

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